2-丁基-5-(邻甲苯基)噻吩 | 1044231-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-丁基-5-(邻甲苯基)噻吩
• 英文名称: 2-butyl-5-(o-tolyl)thiophene
• 英文别名: 5-butyl-2-o-tolylthiophene；2-n-butyl-5-o-tolylthiophene；5-Butyl-2-o-tolylthiophene；2-butyl-5-(2-methylphenyl)thiophene
• CAS: 1044231-44-8
• 化学式: C₁₅H₁₈S
• 分子量: 230.374
• InChiKey: MCWUTRIMHNKSRM-UHFFFAOYSA-N

物化性质

• 沸点：
  310.2±11.0 °C(predicted)
• 密度：
  1.017±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 2-(2-methylphenyl)thiophene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到2-丁基-5-(邻甲苯基)噻吩
  参考文献：
  名称：

  Alkylated 2,2′-bithiophenes and 2-phenylthiophenes in the composition of pyrolysis products of high-sulfur kerogen

  摘要：

  Compounds from the 5-n-alkyl-2,2'-bithiophene, 5-n-alkyl-5'-methyl-2,2'-bithiophene, 5-n-alkyl-2-phenylthiophene, and 5-n-alkyl-2-o-tolylthiophene homologous series were synthesized to prove their presence in the pyrolysis products of sulfur-rich kerogen. A study of the pyrolysis products of sulfur-vulcanized polybutadiene confirmed that these compounds can be formed via the thermal transformation of n-alkyl polysulfur-bound fragments of sulfur-rich kerogen. The earlier proposed scheme that assumes the dependence of the composition of the pyrolysis products of sulfur-rich kerogen on its saturation with sulfide bridges was experimentally corroborated.

  DOI：

  10.1134/s0965544107030061

文献信息

• Ligand-less palladium-catalyzed direct 5-arylation of thiophenes at low catalyst loadings
  作者：Julien Roger、Franc Požgan、Henri Doucet

  DOI：10.1039/b819912d

  日期：——

  Ligand-less Pd(OAc)2 provides a very efficient catalyst for the direct 5-arylation of thiophene derivatives. With this catalyst, a low palladium concentration (0.1–0.001 mol%) should be employed in order to obtain high yields of coupling products. At higher concentrations a fast formation of inactive “Pd black” generally occurs. Substrates/catalysts ratios up to 100000 can be employed with the most

  配体较少的Pd（OAc）2提供了非常有效的催化剂 用于直接的5-芳基化 噻吩衍生品。有了这个催化剂低 钯为了获得高收率的偶联产物，应使用浓度（0.1–0.001 mol％）的溶液。在较高浓度下，通常会快速形成无活性的“钯黑”。基材/催化剂活性最高的芳基溴化物可使用高达100000的比例。两个偶合伙伴都可以容忍各种各样的官能团。该反应的主要浪费是与KOAc有关的HBr。因此，该方法比采用有机金属衍生物的传统交叉偶联方法在经济和环境上更具吸引力。
• Direct Arylation of Thiophenesvia Palladium-Catalysed CH Functionalisation at Low Catalyst Loadings
  作者：Ahmed Battace、Mhamed Lemhadri、Touriya Zair、Henri Doucet、Maurice Santelli

  DOI：10.1002/adsc.200700142

  日期：2007.11.5

  Palladium associated with cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane (Tedicyp) was found to promote the direct 2-arylation of a variety of thiophene derivatives via CH functionalisation in good yields using very low catalyst loadings. Electron-deficient, electron-excessive or sterically-congested aryl bromides are tolerated. Moreover, several substituents on the aryl bromide

  关联钯顺，顺，顺-1,2,3,4- -四（二苯基膦基）环戊烷（Tedicyp）被发现，以促进各种噻吩衍生物的直接2-芳基化通过以良好的收率CH官能使用非常低的催化剂加载。可以耐受电子不足，电子过量或空间拥挤的芳基溴化物。此外，在芳基溴或噻吩衍生物上的几个取代基如乙酰基，甲酰基，腈，硝基，酯，甲氧基，氟或三氟甲基是可容忍的。使用低至0.1-0.01 mol％的催化剂，将反应性最强的芳基溴化物与噻吩衍生物偶联。
• Direct Arylation of Heteroaromatic Compounds with Congested, Functionalised Aryl Bromides at Low Palladium/Triphosphane Catalyst Loading
  作者：David Roy、Sophal Mom、Dominique Lucas、Hélène Cattey、Jean‐Cyrille Hierso、Henri Doucet

  DOI：10.1002/chem.201100100

  日期：2011.5.27

  A new ferrocenyl triphosphane ligand associated to palladium was found to be an efficient catalyst for the direct coupling of highly congested, functionalised aryl bromides with a variety of heteroarenes. These coupling reactions can generally be performed by using a low‐loading (0.1–0.5 mol %) of the catalyst. The present protocol tolerates important and useful functional groups, which allows for

  发现与钯缔合的新的二茂铁基三膦配体是将高度拥挤的，官能化的芳基溴化物与各种杂芳烃直接偶联的有效催化剂。这些偶联反应通常可以通过使用低负荷（0.1–0.5 mol％）的催化剂来进行。本方案耐受重要且有用的官能团，其允许进一步加工成更复杂的杂环分子。杂芳族化合物与拥挤的邻位取代的芳基溴化物的直接芳基化可能仅需几个步骤，即可进一步聚合各种配体，生物活性分子和分子材料。
• Alkylated 2,2′-bithiophenes and 2-phenylthiophenes in the composition of pyrolysis products of high-sulfur kerogen
  作者：D. A. Bushnev

  DOI：10.1134/s0965544107030061

  日期：2007.5

  Compounds from the 5-n-alkyl-2,2'-bithiophene, 5-n-alkyl-5'-methyl-2,2'-bithiophene, 5-n-alkyl-2-phenylthiophene, and 5-n-alkyl-2-o-tolylthiophene homologous series were synthesized to prove their presence in the pyrolysis products of sulfur-rich kerogen. A study of the pyrolysis products of sulfur-vulcanized polybutadiene confirmed that these compounds can be formed via the thermal transformation of n-alkyl polysulfur-bound fragments of sulfur-rich kerogen. The earlier proposed scheme that assumes the dependence of the composition of the pyrolysis products of sulfur-rich kerogen on its saturation with sulfide bridges was experimentally corroborated.